Director of Operations/Chief of Staff

One of the fastest growing, disruptive forces in the global employment market; Borderless AI is changing how businesses recruit, retain, and pay talent across the globe. Established in Toronto in 2022, Borderless has development a global payroll platform and Employer of Record (EOR) driven by AI that allows companies to enroll workers and contractors in more than 170 countries without creating foreign entities. Supported by a $27M funding round led by Susquehanna and Aglaé Ventures, Borderless is growing quickly attracting top tier clients like The Ritz-Carlton Yacht Collection, Colligo and WineDirect, revolutionizing how businesses function globally.
  
Alberni, the first AI agent for global Human Resources departments, is at the heart of Borderless. By combining cutting edge technology with committed local knowledge, Alberni automates complicated procedures like employment contract formation, compliance advice, and daily HR operations in a matter of minutes. Borderless can provide real time compliance, cash flow friendly payroll solutions and quicker onboarding (often in as little as five days) using an AI native approach suitable for both start ups and enterprise businesses alike.
  
Borderless AI offers the chance to join a well-funded, high growth team at the forefront of AI and groundbreaking global work. It’s a chance to grow with purpose, speed and scale while also influencing the future direction of hiring internationally.
  
Role:

Borderless is seeking an experienced and highly capable Chief of Staff to serve as a strategic and operational partner to the CEO and Executive Leadership Team. This critical role will be instrumental in driving organizational effectiveness, operational excellence, and alignment across the enterprise. The Chief of Staff will act as a force multiplier for the leadership team, ensuring strategic initiatives are executed with precision while enabling the company to scale efficiently.
  
An outstanding operator with a proven track record in cross-functional leadership, process optimization, and business management is the ideal candidate. To drive execution, they are equally at ease engaging at a strategic level and delving deeply into the operational details.
  
Responsibilities:
  
Strategic Operational Leadership

• Assist the [CEO/ELT] in developing and carrying out the organization's strategic and operational initiatives by acting as a valued advisor and thinking partner.
• Convert high-level strategies into workable plans while making sure that all business units are moving in the same direction.
• Track performance in relation to operational KPIs and important goals, recognizing hazards and suggesting fixes.

Program & Project Management

• Oversee and direct cross-functional projects that promote business expansion and operational effectiveness.
• Create and put into place project management frameworks to monitor and document the status of important projects.

Operational Excellence

• Evaluate and upgrade internal workflows and processes to increase efficacy and scalability.
• Encourage accountability by putting in place procedures and frameworks for reporting and performance management.
• Streamline departmental and team-wide operational planning and resource allocation.

Leadership Enablement & Communication

• Serve as a bridge between the executive leadership team and the broader organization, ensuring effective communication and alignment.
• Create the reports, dashboards, and documents needed for strategic reviews, leadership offsites, and board meetings.
• Assist leadership in making decisions by obtaining, evaluating, and presenting important information.

Qualifications:

• Minimum 7-10 years of progressive roles focused on strategy, operations, or business management, ideally within a scaling, early-stage business.
• Proven track record of successfully leading cross-functional initiatives.
• Experience working closely with senior executives and/or board members.
• Prior experience in consulting, operational leadership, or a Chief of Staff role preferred.

Competencies:

• Exceptional operational and strategic thinking skills. You can make connections across complex systems.
• Excellent project management and organizational abilities; thrives in a fast-paced, high-growth environment.
• Strong analytical skills with a data-driven approach to decision-making.
• Excellent interpersonal, communication, and influencing skills; capable of fostering trust across all levels of an organization.
• Adaptability and comfort with ambiguity in a rapidly changing environment.